Chianti, Tuscany

Overview

Discover Chianti: Private Tours, Experiences & Custom Travel

If you have ever believed in fairy-tales and landscapes where Kings and Queens ruled beautiful country-sides adorned with vineyards and picturesque gardens at every corner, the Chianti region is for you!

Many people ask what is the "Chianti"? There are no borders here, it is an un-spoken territory, in the Tuscan countryside between Siena and Florence, that has no precise name. No name is necessary, because when you enter the borders here, you will know very clearly that you in Chianti when the names on signs like Radda - Greve - Panzano - Castellina - and many others you will see, all end with the word Chianti!

The Chianti region comprises numerous towns, all once Medieval settlements, with castles, villas, old mills, fortifications and farmsteads. Among the popular events, the Palio horse race of Siena is perhaps the best known, although the numerous smaller scale wine Festivals, markets, and concerts organized in the castles should not be missed.

Chianti is an unspoilt land with a patchwork of meadows and fields where the famous blue-violet Iris grow wild, (the flower which was chosen as symbol of Florence and used for centuries in perfumes). Articles in Terracotta are still produced by local craftsmen.

Its natural environment is its fortune: Chianti is a splendid countryside which stretches from Florence to Siena, over great expanses of vineyards resting on the hillside from where the famous red wine is exported throughout the world.

The region's game dishes of wild boar, quail and pigeon accompanied by wild mushrooms are as famous as the area's cold meats, Chianina beef and Cinta Senese pork. The countryside is also characterized by its olive groves which produce a highly acclaimed oil.

Plan Your Experience

Explore Chianti

Chianti in pictures

Gallery

A few frames from our own trips. The rest are in the gallery below.

Chianti Simple Pleasures

Chianti, Tuscany Italy

Chianti, Italy - vineyards in spring time

Experience Greve in Chianti Italy

Via ferruccio 18 castellina in chianti Italy

Map

Get your bearings before you go

Multi-Day Holidays Tours

Whole journeys, planned end to end

Florence, Tuscany and the Italian Riviera

A classic introduction to the must-see sites of Tuscany and Cinque Terre. From the wine-growing lands of Chianti and Val d'Orcia to the Renaissance splendour and the museums of Florence, the tour ends in the incredible natural beauty of the Italian...

Private

10 Days / 9 Nights

Wine Estates, Culture and Fun in Tuscany and the Cinque Terre!

This 9 night/10 day tour begins in Rome and includes some of Italy's most incredible Etruscan towns, hot-springs and forgotten (though incredibly beautiful) coastal areas that few visitors to Italy ever experience. Highlights of the tour include sta...

Private

10 Days / 9 Nights

Tuscany & Umbria: Exclusive Small Group Tour Including Florence

This deluxe small group (or private tour ) through Tuscany and Umbria in central Italy offers our guests the possibility to experience two of Italy's most beautiful wine regions as well as Florence. There are many highlights on this tour including a...

Semi-Private

7 Days / 6 Nights

Private & Small Group Tours in Chianti

Days out with people who know the way

If you're spending your holidays in Tuscany, or even just passing through, do not miss the opportunity to learn more about one of the most mysterious ingredients of Italian cuisine: The Truffle! Have fun hunting in the woods with the truffle-dogs, t...

★ ★ ★ ★

Used as the set for famous costume films and supposed birthplace of Mona Lisa, Vignamaggio offers un...

Business Centre +9 more

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Villas

Private homes with stories of their own

Italy,Tuscany,Chianti

Villa

Villa Castrum

5-7 Beds 10-14

Air Conditioning +4 more

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Photo Gallery

Castellina in Chianti

Panzano in Chianti

Castellina in Chianti

8 Beds 16

Air Conditioning +12 more

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Cottage Fienile featured rental property in Chianti

Italy,Tuscany,Siena (SI),Castellina in Chianti

Estate

Cottage Fienile

Air Conditioning +10 more

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Italy,Tuscany,Lucca

Villa

Gorgeous villa near Lucca

3 Beds 6

Balcony +11 more

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Popular Transfer Routes in Chianti

The rides our guests ask for most, with a driver who knows the way.

Italy Vacation Specialists provides licensed private transfer services throughout Italy, including Chianti and surrounding areas. With over 20 years of experience, our professional English-speaking drivers offer both Business Class and Luxury Class vehicles for airport transfers, city-to-city rides, and full-day chauffeur services. All vehicles are fully insured, well-maintained, and operated by vetted local drivers who know the roads, traffic patterns, and best routes across the region.

Rome Florence

Private Transfer

Rome Naples

Private Transfer

Rome Venice

Private Transfer

Florence Venice

Private Transfer

Milan Venice

Private Transfer

Naples Amalfi

Private Transfer

Rome Amalfi

Private Transfer

Milan Lake Como

Private Transfer

Florence Siena

Private Transfer

Naples Sorrento

Private Transfer

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In their words

Stories That Stay With You

Here's what our guests share about their unforgettable journeys

“The trip was great; we appreciate all the hard work you and your team invested to make our experience a once in a lifetime trip. We appreciate all the attention to the details, in particular Giuseppe spending the time and the focus with us on the road and as w…”
Leon and Michele Read their story

“I went to high school with the owner of the company who organized my honeymoon for myself and my now wife from Tokyo. We spent three short weeks seeing Piedmont and experiencing wine paradise there, then heading to Nice in France with our private driver and fl…”
Robin and Kumi Bruun, Tokyo Japan Read their story

“I am a travel agent from Lebanon and have organized several group tours as well as individual tours of Italy with Italy Vacation Specialists. I highly recommend them as one of the very best tour operators in Italy to work with, given their professionalism and…”
Nicole Haddad, Lebanese Travel Agent Read their story

“Jesse, There are no words to describe the fabulous time we had in Italy. Everything went as you promised. Absolutely no problems! The venues were fabulous. The guides were punctual and helpful. It couldn't have worked out better. You and your staff deserve hig…”
Jo Ann West Read their story

“I have traveled to Italy 2x with the IVS for my own pleasure trips and 2x for business with IVS. These guys really pay attention and make your trip go like clockwork. Italy is nuts, just saying! There are so many rules and restrictions now, so we did not want…”
JoAnne Beaudoin, Retired Nurse Read their story

“In September of 2018 I brought a group of 12 from Venice to Sicily and organized all of my services with the Italy Vacation Specialists. Being a travel agent and in the business, I know how complicated organizing travel arrangements can be in Italy and the IVS…”
Ann Brownell, KHM Travel Group Read their story